Compound for organic electric element, organic electric element using the same, and electronic device thereof

ABSTRACT

Provided is a compound capable of improving luminous efficiency, stability and lifetime of an organic electronic device, an organic electric element using the same, and an electronic device comprising the element.

BACKGROUND Technical Field

The present invention relates to compound for organic electric element,organic electric element using the same, and an electronic devicethereof.

Background Art

In general, organic light emitting phenomenon refers to a phenomenonthat converts electric energy into light energy by using an organicmaterial. An organic electric element using an organic light emittingphenomenon usually has a structure including an anode, a cathode, and anorganic material layer interposed therebetween. Here, in order toincrease the efficiency and stability of the organic electronic element,the organic material layer is often composed of a multi-layeredstructure composed of different materials, and for example, may includea hole injection layer, a hole transport layer, an emitting layer, anelectron transport layer, an electron injection layer and the like.

A material used as an organic material layer in an organic electricelement may be classified into a light emitting material and a chargetransport material, such as a hole injection material, a hole transportmaterial, an electron transport material, an electron injection materialand the like depending on its function.

And the light emitting material may be classified into a polymer typeand a low molecular type depending on the molecular weight, and into afluorescent material derived from the singlet excited state of electronsand a phosphorescent material derived from the triplet excited state ofelectrons depending on the light emitting mechanism. Further, the lightemitting material can be classified into blue, green, and red lightemitting materials and yellow and orange light emitting materialsnecessary for realizing better natural color depending on theluminescent color.

Meanwhile, when only one material is used as a light emitting material,there arises a problem that the maximum light emission wavelength shiftsto a long wavelength due to intermolecular interaction, the color puritydrops, or the efficiency of the device decreases due to the lightemission attenuation effect, therefore a host/dopant system can be usedas a light emitting material in order to increase luminous efficiencythrough increase of color purity and energy transfer. When the smallamount of dopant having a smaller energy band gap than the host formingthe emitting layer is mixed on the emitting layer, the excitonsgenerated in the emitting layer are transported to the dopant to emitlight with high efficiency. At this time, since the wavelength of thehost is shifted to the wavelength band of the dopant, light of a desiredwavelength can be obtained depending on the type of the dopant used.

Currently, the portable display market is growing in size as alarge-area display, which requires more power than the power consumptionrequired by existing portable displays. Therefore, power consumption isa very important factor for portable displays, which have a limitedpower source, such as a battery, and efficiency and lifetime issues mustbe solved.

Efficiency, life span, driving voltage and the like are related to eachother. As the efficiency is increased, the driving voltage is relativelydecreased, and as the driving voltage drops, the crystallization of theorganic material due to joule heating generated during driving isreduced, and as a result, the life span tends to increase.

However, simply improving the organic material layer cannot maximize theefficiency. This is because, when the optimal combination of the energylevel and T1 value between each organic material layer and the intrinsicproperties (mobility, interface characteristics, etc.) of the materialare achieved, long life and high efficiency can be achieved at the sametime. Therefore, it is necessary to develop a light emitting materialhaving a high thermal stability and achieving a charge balance in theemitting layer efficiently.

That is, in order to sufficiently exhibit the excellent characteristicsof the organic electric element, a material for forming an organicmaterial layer in an element such as a hole injection material, a holetransport material, a light emitting material, an electron transportmaterial, an electron injection material, an emitting-auxiliary layermaterial, and the like should be supported by stable and efficientmaterials. However, such a stable and efficient organic material layermaterial for an organic electric element has not been sufficientlydeveloped yet. Therefore, development of new materials is continuouslyrequired, and especially development of host materials for the emittinglayer is urgently required.

Otherwise, in the case of a polycyclic compound including a heteroatom,the difference in properties according to the material structure is solarge that it is applied to various layers as OLED material. Inparticular, it has characteristics of different band gaps (HOMO, LUMO),electrical characteristics, chemical properties, and physical propertiesdepending on the number of rings, fused positions and the type andarrangement of heteroatoms, therefore application development forvarious OLED layers using the same has been progressed. Recently,development of OLED material for heteroatom type, number and position ofpentacyclic compounds has been actively developed.

As a precedent reference, U.S. Pat. No. 8,334,058 B2 is referred to.

DETAILED DESCRIPTION OF THE INVENTION Summary

Using the characteristics of the polycyclic compound, the presentinvention provides a compound capable of maximizing the effect ofimproving luminous efficiency and long life, while maintaining orslightly reducing the driving voltage of the device, and an organicelectric element using the same and an electronic device thereof.

Technical Solution

The present invention provides compounds represented by Formula (1) andFormula (18), organic electric elements comprising the same andelectronic devices thereof.

Effects of the Invention

By using the compound according to the present invention, it is possibleto achieve a high luminous efficiency, a low driving voltage, and a highheat resistance of the element, and can greatly improve the color purityand lifetime of the element.

BRIEF DESCRIPTION OF THE DRAWINGS [16] The FIG. illustrates an exampleof an organic electric element according to the present invention. [17]100: organic electric element, 110: substrate [18] 120: the firstelectrode (anode), 130: the hole injection layer [19] 140: the holetransport layer, 141: a buffer layer [20] 150: the emitting layer, 151:the emitting auxiliary layer [21] 160: the electron transport layer,170: the electron injection layer [22] 180: the second electrode(cathode)

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif a component is described as being “connected”, “coupled”, or“connected” to another component, the component may be directlyconnected or connected to the other component, but another component maybe “connected”, “coupled” or “connected” between each component.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen”, as used herein,includes fluorine, bromine, chlorine, or iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group”, as usedherein, has a single bond of 1 to 60 carbon atoms, and means saturatedaliphatic functional radicals including a linear alkyl group, a branchedchain alkyl group, a cycloalkyl group (alicyclic), an cycloalkyl groupsubstituted with a alkyl or an alkyl group substituted with acycloalkyl.

Unless otherwise stated, the term “haloalkyl” or “halogen alkyl”, asused herein, includes an alkyl group substituted with a halogen.

Unless otherwise stated, the term “heteroalkyl”, as used herein, meansalkyl substituted one or more of carbon atoms consisting of an alkylwith heteroatom.

Unless otherwise stated, the term “alkenyl” or “alkynyl”, as usedherein, has double or triple bonds of 2 to 60 carbon atoms, but is notlimited thereto, and includes a linear or a branched chain group.

Unless otherwise stated, the term “cycloalkyl”, as used herein, meansalkyl forming a ring having 3 to 60 carbon atoms, but is not limitedthereto.

Unless otherwise stated, the term “alkoxyl group”, “alkoxy group” or“alkyloxy group”, as used herein, means an oxygen radical attached to analkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.

Unless otherwise stated, the term “alkenoxyl group”, “alkenoxy group”,“alkenyloxyl group” or “alkenyloxy group”, as used herein, means anoxygen radical attached to an alkenyl group, but is not limited thereto,and has 2 to 60 carbon atoms.

Unless otherwise stated, the term “aryloxyl group” or “aryloxy group”,as used herein, means an oxygen radical attached to an aryl group, butis not limited thereto, and has 6 to 60 carbon atoms.

Unless otherwise stated, the term “aryl group” or “arylene group”, asused herein, has 6 to 60 carbon atoms, but is not limited thereto.Herein, the aryl group or arylene group means a monocyclic andpolycyclic aromatic group, and may also be formed in conjunction with anadjacent group. Examples of “aryl group” may include a phenyl group, abiphenyl group, a fluorene group, or a spirofluorene group.

The prefix “aryl” or “ar” means a radical substituted with an arylgroup. For example, an arylalkyl may be an alkyl substituted with anaryl, and an arylalenyl may be an alkenyl substituted with aryl, and aradical substituted with an aryl has a number of carbon atoms as definedherein.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an arylalkoxymeans an alkoxy substituted with an aryl, an alkoxylcarbonyl means acarbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl alsomeans an alkenyl substituted with an arylcarbonyl, wherein thearylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “heteroalkyl”, as used herein, meansalkyl including one or more of heteroatoms. Unless otherwise stated, theterm “heteroaryl group” or “heteroarylene group”, as used herein, meansa C2 to C60 aryl including one or more of heteroatoms or arylene group,but is not limited thereto, and includes at least one of monocyclic andpolycyclic rings, and may also be formed in conjunction with an adjacentgroup.

Unless otherwise stated, the term “heterocyclic group”, as used herein,contains one or more heteroatoms, but is not limited thereto, has 2 to60 carbon atoms, includes any one of monocyclic and polycyclic rings,and may include heteroaliphadic ring and/or heteroaromatic ring. Also,the heterocyclic group may also be formed in conjunction with anadjacent group.

Unless otherwise stated, the term “heteroatom”, as used herein,represents at least one of N, O, S, P, or Si.

Also, the term “heterocyclic group” may include a ring including SO₂instead of carbon consisting of cycle. For example, “heterocyclic group”includes compound below.

Unless otherwise stated, the term “aliphatic”, as used herein, means analiphatic hydrocarbon having 1 to 60 carbon atoms, and the term“aliphatic ring”, as used herein, means an aliphatic hydrocarbon ringhaving 3 to 60 carbon atoms.

Unless otherwise stated, the term “ring”, as used herein, means analiphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6to 60 carbon atoms, or a hetero ring having 2 to 60 carbon atoms, or afused ring formed by the combination of them, and includes a saturatedor unsaturated ring.

Other hetero compounds or hetero radicals other than the above-mentionedhetero compounds include, but are not limited thereto, one or moreheteroatoms.

Unless otherwise stated, the term “carbonyl”, as used herein, isrepresented by —COR′, wherein R′ may be hydrogen, an alkyl having 1 to20 carbon atoms, an aryl having 6 to 30 carbon atoms, a cycloalkylhaving 3 to 30 carbon atoms, an alkenyl having 2 to 20 carbon atoms, analkynyl having 2 to 20 carbon atoms, or the combination of these.

Unless otherwise stated, the term “ether”, as used herein, isrepresented by —R—O—R′, wherein R or R′ may be independently hydrogen,an alkyl having 1 to 20 carbon atoms, an aryl having 6 to 30 carbonatoms, a cycloalkyl having 3 to 30 carbon atoms, an alkenyl having 2 to20 carbon atoms, an alkynyl having 2 to 20 carbon atoms, or thecombination of these.

Unless otherwise stated, the term “substituted or unsubstituted”, asused herein, means that substitution is substituted by at least onesubstituent selected from the group consisting of, but is not limitedthereto, deuterium, halogen, an amino group, a nitrile group, a nitrogroup, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkylaminegroup, a C₁-C₂₀ alkylthiopen group, a C₆-C₂₀ arylthiopen group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, aC₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, aC₈-C₂₀ arylalkenyl group, a silane group, a boron group, a germaniumgroup, and a C₂-C₂₀ heterocyclic group.

Unless otherwise expressly stated, the Formula used in the presentinvention, as used herein, is applied in the same manner as thesubstituent definition according to the definition of the exponent ofthe following Formula.

Wherein, when a is an integer of zero, it means the substituent R¹ isabsent. That is, when a is 0, it means that all the carbons forming thebenzene ring are bonded to hydrogen. In this case, the sign of thehydrogen bonded to the carbon may be omitted and the formula or compoundmay be described. When a is an integer of 1, the sole substituent R¹ islinked to any one of the carbon constituting the benzene ring, when a isan integer of 2 or 3, they are respectively bonded as follows, in whichR¹ may be the same as or different from each other, and when a is aninteger of 4 to 6, and it is bonded to the carbon of the benzene ring ina similar manner, whereas the indication of hydrogen bonded to thecarbon forming the benzene ring is omitted.

Hereinafter, a compound according to an aspect of the present inventionand an organic electric element comprising the same will be described.

According to a specific example of the present invention, there isprovided a compound represented by Formula (1).

{In Formula (1),

1) Ar¹, Ar² and Ar³ are each independently a C₆-C₆₀ aryl group;2) l+e is an integer of 0 to 4, d+m is an integer of 0 to 4, a and b arean integer of 0 to 3, n is an integer of 1 to 3, c is an integer of 0 to4,3) R¹, R², R³, R⁴ and R⁵ are each independently selected from the groupconsisting of hydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; afluorenyl group; a C₂-C₆₀ heterocyclic group including at least oneheteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphaticring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenylgroup; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxygroup; and -L′-N(R_(a))(R_(b));wherein, L′ may be selected from the group consisting of a single bond;a C₆-C₆₀ arylene group; a fluorenylene group; a fused ring group of aC₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀heterocyclic group;and the R_(a) and R_(b) are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group; a fluorenyl group; a fused ring groupof a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀heterocyclic group including at least one heteroatom of O, N, S, Si, orP; or a plurality of R¹, a plurality of R², a plurality of R³, aplurality of R⁴, and a plurality of R⁵ may be bonded to each other toform an aromatic ring or and heteroaromatic ring,

wherein, the aryl group, fluorenyl group, arylene group, heterocyclicgroup, fluorenylene group, fused ring group, alkyl group, alkenyl group,alkoxy group and aryloxy group may be substituted with one or moresubstituents selected from the group consisting of deuterium; halogen;silane group; siloxane group; boron group; germanium group; cyano group;nitro group; C₁-C₂₀ alkylthio group; C₁-C₂₀ alkoxyl group; C₁-C₂₀ alkylgroup; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group; C₆-C₂₀ aryl group;C₆-C₂₀ aryl group substituted with deuterium; a fluorenyl group; C₂-C₂₀heterocyclic group; C₃-C₂₀ cycloalkyl group; C₇-C₂₀ arylalkyl group andC₈-C₂₀ arylalkenyl group, wherein the substituents may be bonded to eachother to form a ring, wherein the term ‘ring’ means a C₃-C₆₀ aliphaticring or a C₆-C₆₀ aromatic ring or a C₂-C₆₀ heterocyclic group or a fusedring formed by the combination thereof and comprises a saturated orunsaturated ring.}

In a specific aspect of the invention, the compound represented byFormula (1) comprises a compound represented by any of Formulas (2) to(7) below.

{In Formulas (2) to (7), Ar¹, Ar², Ar³, l, m, n, a, b, c, d, e, R¹, R²,R³, R⁴ and R⁵ are the same as defined above.}

Preferably, at least one of Ar¹, Ar², and R³ in Formula (1) comprises aC₆˜C₂₄ aryl group, more preferably, Ar¹ or Ar³ in Formula (1) comprisesa C₆-˜₂₄ aryl group.

Also, R³ in Formula (1) is a C₆˜C₂₄ aryl group.

Also, Formula (1) comprises a compound represented by any of thefollowing Formulas (8) to (10)

{In Formulas (8) to (10), Ar¹, Ar², Ar³, l, m, n, a, b, c, d, e, R¹, R²,R³, R⁴ and R⁵ are the same as defined above.}

Also, the compound represented by Formula (1) comprises compoundsrepresented by Formula (11)

{In Formula (11), Ar¹, Ar², Ar³, l, m, n, a, b, c, d, e, R¹, R², R³, R⁴and R⁵ are the same as defined above.}

Specifically, in the present invention, the compound represented byFormula (1) includes the following compounds P-1 to P-160.

In another aspect, the present invention provides an organic electricelement comprising a first electrode; a second electrode; and an organicmaterial layer disposed between the first electrode and the secondelectrode and including a compound included in Formula (1).

Wherein the organic material layer comprises at least one of a holeinjection layer, a hole transport layer, an emitting auxiliary layer, anemitting layer, an electron transport auxiliary layer, an electrontransport layer and an electron injection layer, wherein at least one ofthe hole injection layer, the hole transport layer, the emittingauxiliary layer, the emitting layer, the electron transport auxiliarylayer, the electron transport layer and the electron injection layercomprises one compound or 2 or more compounds of Formula (1).Preferably, the compound is included in the emitting layer.

More specifically, the present invention provides an organic electronicelement further comprising a compound represented by Formula (12) in theemitting layer.

{In Formula (12),

1) Z¹, Z², Z³, Z⁴, Z⁵, Z⁶, Z⁷, Z⁸, Z⁹, Z¹⁰, Z¹¹, Z¹², Z¹³, Z¹⁴, Z¹⁵ andZ¹⁶ are each independently CR or N,wherein R is hydrogen; a C₆-C₆₀ aryl group; a C₃-C₆₀ heterocyclic groupincluding at least one heteroatom of O, N, S, Si, or P; a C₁-C₅₀ alkylgroup; a C₆-C₆₀ arylamine group; a fluorene group; and is possible toform a ring by combining with neighboring groups,2) L² is selected from the group consisting of a single bond; a C₆-C₆₀arylene group; a C₃-C₆₀ heteroarylene group; and a divalent aliphatichydrocarbon group;

3) W is NAr⁵, O, S or CR′R″;

R′ and R″ are each independently selected from the group of a C₁-C₅₀alkyl group; a C₆-C₆₀ aryl group; a C₃-C₆₀ heterocyclic group includingat least one heteroatom of O, N, S, Si, or P; and R′ and R″ may bebonded to each other to form a spiro.4) Ar⁴ and Ar⁵ are each independently selected from the group consistingof a C₆-C₆₀ aryl group; a C₃-C₆₀ heterocyclic group including at leastone heteroatom of O, N, S, Si, or P; a C₁-C₅₀ alkyl group; a C₆-C₆₀arylamine group; a fluorene group}

Formula (12) comprises a compound represented by any of the followingFormulas (13) to (16).

{In Formulas (13) to (16), Ar⁴, Ar⁵, Z¹, Z², Z³, Z⁴, Z⁵, Z⁶, Z⁷, Z⁸, Z⁹,Z¹⁰, Z¹¹, Z¹², Z¹³, Z¹⁴, Z¹⁵, Z¹⁶, L², R′, R″ are the same as definedabove.}

Preferably, both Ar⁴ and Ar⁵ of Formula (12) comprise a compoundrepresented by a C₆-C₃₀ aryl group.

Also, the compound represented by Formula (12) comprises a compoundrepresented by Formula (17)

{In Formula (17), Ar⁴, Ar⁵, Z¹, Z², Z³, Z⁴, Z⁵, Z⁶, Z⁷, Z⁸, Z⁹, Z¹⁰,Z¹¹, Z¹², Z¹³, Z¹⁴, Z¹⁵, Z¹⁶, and L² are the same as defined above.

1) L¹ is selected from the group of a single bond; a C₆-C₆₀ arylenegroup; a C₃-C₆₀ heteroarylene group; and a divalent aliphatichydrocarbon group;

2) Y is O, S or NAr⁵,

3) R^(a) and R^(b) are each independently selected from the groupconsisting of hydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; afluorenyl group; a C₂-C₆₀ heterocyclic group including at least oneheteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphaticring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenylgroup; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxygroup; and -L′-N(R_(a))(R_(b)); or a plurality of R^(a) and a pluralityof R^(b) may be bonded to each other to form an aromatic ring or andheteroaromatic ring,4) y is an integer of 0 to 3, and z is an integer of 0 to 4}

Specifically, the compound represented by Formula (12) comprises thefollowing compounds 4-1 to 4-52

As another example, the present invention provides an organic electronicelement comprising an anode; a cathode; an organic material layer formedbetween the anode and the cathode; wherein the organic material layerincludes an emitting layer, an hole transport layer formed between theanode and the emitting layer; an emitting auxiliary layer formed betweenthe emitting layer and the hole transport layer; wherein the holetransport layer or the emitting auxiliary layer comprises a compoundrepresented by Formula (18), and the emitting layer comprises a compoundrepresented by Formula (1).

{In Formula (1) and Formula (18),

1) Ar, Ar², Ar³, l, m, n, a, b, c, d, e, R¹, R², R³, R⁴ and R⁵ are thesame as defined above.}2) Ar⁴ and Ar⁵ are each independently selected from the group consistingof a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic groupincluding at least one heteroatom of O, N, S, Si or P; a fused ringgroup of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b));

wherein, L′ may be selected from the group consisting of a single bond;a C₆-C₆₀ arylene group; a fluorenylene group; a fused ring group of aC₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀heterocyclic group;

and the R_(a) and R_(b) are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group; a fluorenyl group; a fused ring groupof a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀heterocyclic group including at least one heteroatom of O, N, S, Si, orP;or Ar⁴ and Ar⁵ may be bonded to each other to form a ring.3) Ar⁶ is selected from the group consisting of a C₆-C₆₀ aryl group; afluorenyl group; a C₂-C₆₀ heterocyclic group including at least oneheteroatom of O, N, S, Si, or P; or is at least one of the followingFormulas (1-a), (1-b), (1-c)

4) Ar⁹, Ar¹⁰ and Ar¹¹ are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀heterocyclic group including at least one heteroatom of O, N, S, Si, orP; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromaticring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynylgroup; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and-L′-N(R_(a))(R_(b));5) h, i and g are an integer of 0 to 4; j is an integer of 0 to 3; R⁶,R⁷, R⁶ and R⁹ are the same or different from each other, and are eachindependently selected from the group consisting of hydrogen; deuterium;halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclicgroup including at least one heteroatom of O, N, S, Si or P; a fusedring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; aC₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; aC₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b));

wherein in case g, h, i, j are 2 or more, R⁶, R⁷, R⁸ and R⁹ are each inplural being the same or different, and may be bonded to each other toform a ring,

6) L⁶ is selected from the group consisting of a single bond; a C₆-C₆₀arylene group; a fluorenylene group; a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclicgroup including at least one heteroatom of O, N, S, Si or P;7) L⁵ is selected from the group consisting of a C₆-C₆₀ arylene group; afluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group including at leastone heteroatom of O, N, S, Si or P}

The present invention also provides an organic electronic elementincluding at least one compound represented by Formula (12) in theemitting layer.

Also, the hole transport layer comprises a compound represented byFormula (19) or Formula (20), and the emitting auxiliary layer comprisesa compound represented by Formula (21) or Formula (22)

{In Formulas (19) to (22),

1) Ar⁶ is selected from the group consisting of a C₆-C₆₀ aryl group; afluorenyl group; a C₂-C₆₀ heterocyclic group including at least oneheteroatom of O, N, S, Si or P;2) Ar⁴, Ar⁵, Ar⁹, Ar¹⁰, Ar¹¹, h, i, g, L, L⁶, R⁶, R⁷, R⁸ and R⁹ are thesame as defined above.}

Specifically, the compound represented by Formula (18) comprises thefollowing compounds 13-1 to 13-79 and compounds 2-1 to 2-76.

As another example, the present invention provides an organic electronicelement comprising an anode; a cathode; an organic material layer formedbetween the anode and the cathode; wherein the organic material layerincludes an emitting layer, an hole transport layer formed between theanode and the emitting layer; an emitting auxiliary layer or an electronblocking layer (EBL) formed between the emitting layer and the holetransport layer; wherein the emitting auxiliary layer or the electronblocking layer comprises a compound represented by Formula (30).

{In Formula (30),

R²⁰, R²¹, R²², R²³, R²⁴, and R² are each independently selected from thegroup consisting of hydrogen; deuterium; halogen; a C₆-C₃₀ aryl group; afluorenyl group; a C₂-C₃₀ heterocyclic group including at least oneheteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₃₀ aliphaticring and a C₆-C₃₀ aromatic ring; a C₁-C₃₀ alkyl group; a C₂-C₂₀ alkenylgroup; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxygroup; or a plurality of R²⁰, a plurality of R²², a plurality of R²³, aplurality of R²⁴, and a plurality of R²⁵ may be bonded to each other toform an aromatic ring or and heteroaromatic ring,v is an integer of 0 to 3,u, w, x and y are each independently an integer of 0 to 4,Z is an integer of 0 to 5,L²⁰ and L²¹ are each independently a single bond; a C₆-C₃₀ arylenegroup; a C₃-C₃₀ heteroarylene group;Ar²⁰ is a C₆-C₃₀ aryl group; or a C₃-C₃₀ heteroarylene group;

X²⁰ is O, S, NR′ or CR′R″

R′ and R″ are each independently selected from the group of a C₁-C₃₀alkyl group; a C₆-C₃₀ aryl group; a C₃-C₃₀ heterocyclic group includingat least one heteroatom of O, N, S, Si, or P; and R′ and R″ may bebonded to each other to form a spiro.}

In present invention, the compound represented by Formula (30) isrepresented by any of the Formulas (31) to (38)

{In Formulas (31) to (40),

R²⁰, R²¹, R²², R²³, R²⁴, R²⁵, L²⁰, L²¹, Ar²⁰ and X²⁰, u, v, w, x, y andz are the same as defined above.}

In the present invention, the compound represented by Formula (30)comprises the following compounds.

Referring to the FIGURE, the organic electric element (100) according tothe present invention includes a first electrode (120) formed on asubstrate (110), a second electrode (180), and an organic material layerincluding the compound represented by Formula (1) between the firstelectrode (120) and the second electrode (180). Here, the firstelectrode (120) may be an anode (positive electrode), and the secondelectrode (180) may be a cathode (negative electrode). In the case of aninverted organic electric element, the first electrode may be a cathode,and the second electrode may be an anode.

The organic material layer may include a hole injection layer (130), ahole transport layer (140), an emitting layer (150), an emittingauxiliary layer (151), an electron transport layer (160), and anelectron injection layer (170) formed in sequence on the first electrode(120). Here, the remaining layers except the emitting layer (150) maynot be formed. The organic material layer may further include a holeblocking layer, an electron blocking layer, an emitting-auxiliary layer(151), an electron transport auxiliary layer, a buffer layer (141),etc., and the electron transport layer (160) and the like may serve as ahole blocking layer.

Although not shown, the organic electric element according to thepresent invention may further include a protective layer formed on atleast one side of the first and second electrodes, which is a sideopposite to the organic material layer.

Otherwise, even if the same core is used, the band gap, the electricalcharacteristics, the interface characteristics, and the like may varydepending on which substituent is bonded at which position, thereforethe choice of core and the combination of sub-substituents associatedtherewith is also very important, and in particular, when the optimalcombination of energy levels and T1 values and unique properties ofmaterials (mobility, interfacial characteristics, etc.) of each organicmaterial layer is achieved, a long life span and high efficiency can beachieved at the same time.

The organic electroluminescent device according to an embodiment of thepresent invention may be manufactured using a PVD (physical vapordeposition) method. For example, a metal or a metal oxide havingconductivity or an alloy thereof is deposited on a substrate to form acathode, and the organic material layer including the hole injectionlayer (130), the hole transport layer (140), the emitting layer (150),the electron transport layer (160), and the electron injection layer(170) is formed thereon, and then depositing a material usable as acathode thereon can manufacture an organic electroluminescent deviceaccording to an embodiment of the present invention. In addition, anemission auxiliary layer (151) may be further formed between the holetransport layer (140) and the emitting layer (150), and an electrontransport auxiliary layer may be further formed between the emittinglayer (150) and the electron transport layer (160).

As another specific example, the present invention provides an organicelectric element wherein the emitting layer in the organic materiallayer is a phosphorescent light emitting layer.

The compounds represented by Formula (1) and (18) are mixed in a ratioof any one of 1:9 to 9:1 to be included in the emitting layer of theorganic material layer, wherein the compound represented by Formula (12)is further mixed to be included in the emitting layer.

The present invention may further include a light efficiency enhancinglayer formed on at least one of the opposite side to the organicmaterial layer among one side of the first electrode, or one of theopposite side to the organic material layer among one side of the secondelectrode.

As another example, the present invention provides an organic electronicdevice wherein the compound represented by Formula (30) is used in anemitting auxiliary layer or an electron blocking layer and is preferablyincluded in a green emitting auxiliary layer. More specifically, thecompound represented by Formula (39) or Formula (40) is included in thegreen emitting auxiliary layer.

Also, the present invention provides the organic electric elementwherein the organic material layer is formed by one of a spin coatingprocess, a nozzle printing process, an inkjet printing process, a slotcoating process, a dip coating process or a roll-to-roll process, andsince the organic material layer according to the present invention canbe formed by various methods, the scope of the present invention is notlimited by the method of forming the organic material layer.

The organic electric element according to an embodiment of the presentinvention may be a front emission type, a back emission type, or aboth-sided emission type, depending on the material used.

WOLED (White Organic Light Emitting Device) has advantages of highresolution realization and excellent fairness, and can be manufacturedusing conventional LCD color filter technology. Various structures for awhite organic light emitting device mainly used as a backlight devicehave been proposed and patented. Representatively, there areside-by-side arrangement of the radiation part of the R (red), G (green)and B (blue), a stacking method in which R, G, and B emitting layers arelaminated on top and bottom, electroluminescence by the blue (B) organicemitting layer and, by using the light from this, a color conversionmaterial (CCM) method using a photo-luminescence of an inorganicphosphor, etc., and the present invention may be applied to such WOLED.

The present invention also provides an electronic device comprising adisplay device including the organic electric element, and a controlunit for driving the display device.

According to another aspect, the present invention provides an displaydevice wherein the organic electric element is at least one of an OLED,an organic solar cell, an organic photo conductor, an organic transistor(organic TFT) and an element for monochromic or white illumination.Here, the electronic device may be a wired/wireless communicationterminal which is currently used or will be used in the future, andcovers all kinds of electronic devices including a mobile communicationterminal such as a cellular phone, a personal digital assistant (PDA),an electronic dictionary, a point-to-multipoint (PMP), a remotecontroller, a navigation unit, a game player, various kinds of TVs, andvarious kinds of computers.

Hereinafter, Synthesis Examples of the compound represented by Formula(1) and (2) of the present invention and preparation examples of theorganic electric element of the present invention will be described indetail by way of example, but are not limited to the following examples.

Synthesis Example 1

Final product 1 represented by Formula (1) according to the presentinvention is prepared by reacting Core and Sub as shown in ReactionScheme 1 below, but is not limited thereto.

Synthesis Example of Core

The Core of the Reaction Scheme 1 can be synthesized by the reactionpath of the following Reaction Schemes 2, but is not limited thereto.

Synthesis of Inter-1

In a round bottom flask, 2,4,6-trichloro-1,3,5-triazine (50 g, 410.1mmol), phenylboronic acid (83.2 g, 451.1 mmol), Pd(PPh₃)₄ (14.2 g, 12.3mmol), K₂CO₃ (170 g, 1.2 mol), THE (1.3 L) and water (700 ml) were addedand stirred at 90° C. When the reaction was complete, the reactionmixture was extracted with CH₂Cl₂ and water. The organic layer was driedover MgSO₄ and concentrated. The resulting compound was separated bysilicagel column chromatography and recrystallization to obtain 55 g(yield: 60%) of Inter 1.

Synthesis of Core

In a round bottom flask, Inter-1 (10 g, 47 mmol),dibenzo[b,d]furan-3-ylboronic acid (12 g, 51.9 mmol), Pd(PPh₃)₄ (1.6 g,1.4 mmol), K₂CO₃ (20 g, 141 mmol), THE (160 ml), and water (80 ml) wereadded and stirred at 90° C. When the reaction was complete, the reactionmixture was extracted with CH₂Cl₂ and water. The organic layer was driedover MgSO₄ and concentrated. The resulting compound was separated bysilicagel column chromatography and recrystallization to obtain 5.7 g(yield: 53%) of Core 1.

Examples of the Core are as follows, but are not limited thereto. Inaddition, [Table 1] shows FD-MS (Field Desorption-Mass Spectrometry)values of some compounds belonging to Core.

TABLE 1 Compound FD-MS Core 1  m/z = 357.07 (C₂₁H₁₂ClN₃O = 357.80) Core2  m/z = 362.10 (C₂₁H₇D₅ClN₃O = 362.83) Core 3  m/z = 407.08(C₂₅H₁₄ClN₃O = 407.86) Core 4  m/z = 407.08 (C₂₃H₁₄ClN₃O = 407.86) Core5  m/z = 433.10 (C₂₇H₁₆ClN₃O = 433.90) Core 6  m/z = 433.10 (C₂₇H₁₆ClN₃O= 433.90) Core 7  m/z = 433.10 (C₂₇H₁₆ClN₃O = 433.90) Core 8  m/z =457.10 (C₂₉H₁₆ClN₃O = 457.92) Core 9  m/z = 509.13 C₃₃H₂₀ClN₃O = 509.99)Core 10 m/z = 433.10 (C₂₇H₁₆ClN₃O = 433.90) Core 11 m/z = 433.10(C₂₇H₁₆ClN₃O = 433.90) Core 12 m/z = 483.11 (C₃₁H₁₈ClN₃O = 483.96) Core13 m/z = 433.10 (C₂₇H₁₆ClN₃O = 433.90) Core 14 m/z = 483.11 (C₃₁H₁₈ClN₃O= 483.96) Core 15 m/z = 509.13 (C₃₃H₂₀ClN₃O = 509.99) Core 16 m/z =433.10 (C₂₇H₁₆ClN₃O = 433.90) Core 17 m/z = 483.11 (C₃₁H₁₈ClN₃O =483.96) Core 18 m/z = 509.13 (C₃₃H₂₀ClN₃O = 509.99) Core 19 m/z = 433.10(C₂₇H₁₆ClN₃O = 433.90) Core 20 m/z = 438.13 (C₂₇H₁₁D₅ClN₃O = 438.93)

Example of Sub

Examples of Sub are as follows, but are not limited thereto. Inaddition, [Table 2] shows FD-MS (Field Desorption-Mass Spectrometry)values of some compounds belonging to Sub.

TABLE 2 Compound FD-MS Sub 1  m/z = 304.07 (C₁₈H₁₃BO₂S = 304.17) Sub 2 m/z = 304.07 (C₁₈H₁₃BO₂S = 304.17) Sub 3  m/z = 354.09 (C₂₂H₁₅BO₂S =354.23) Sub 4  m/z = 354.09 (C₂₂H₁₅BO₂S = 354.23) Sub 5  m/z = 354.09(C₂₂H₁₅BO₂S = 354.23) Sub 6  m/z = 380.10 (C₂₄H₁₇BO₂S = 380.27) Sub 7 m/z = 404.10 (C₂₆H₁₇BO₂S = 404.29) Sub 8  m/z = 380.10 (C₂₄H₁₇BO₂S =380.27) Sub 9  m/z = 385.14 (C₂₄H₁₂D₅BO₂S = 385.30) Sub 10 m/z = 430.12(C₂₈H₁₉BO₂S = 430.33) Sub 11 m/z = 430.12 (C₂₈H₁₉BO₂S = 430.33) Sub 12m/z = 480.14 (C₃₂H₂₁BO₂S = 480.39) Sub 13 m/z = 456.14 (C₃₀H₂₁BO₂S =456.37) Sub 14 m/z = 456.14 (C₃₀H₂₁BO₂S = 456.37) Sub 15 m/z = 456.14(C₃₀H₂₁BO₂S = 456.37) Sub 16 m/z = 380.10 (C₂₄H₁₇BO₂S = 380.27) Sub 17m/z = 385.14 (C₂₄H₁₂D₅BO₂S = 385.30) Sub 18 m/z = 430.12 (C₂₈H₁₉BO₂S =430.33) Sub 19 m/z = 430.12 (C₂₈H₁₉BO₂S = 430.33) Sub 20 m/z = 480.14(C₃₂H₂₁BO₂S = 480.39) Sub 21 m/z = 456.14 (C₃₀H₂₁BO₂S = 456.37) Sub 22m/z = 456.14 (C₃₀H₂₁BO₂S = 456.37) Sub 23 m/z = 456.14 (C₃₀H₂₁BO₂S =456.37)

Synthesis Example of Product Synthesis Example of P-41

In around bottom flask, Core 2 (5 g, 14 mmol), Sub 1 (4.6 g, 15.2 mmol),Pd(PPh₃)₄ (0.5 g, 0.4 mmol), KCO₃ (5.7 g, 41.3 mmol), TH and water wereadded and stirred at 90° C. When the reaction was complete, the reactionmixture was extracted with CH₂Cl₂ and water. The organic layer was driedover MgSO₄ and concentrated. The resulting compound was separated bysilicagel column chromatography and recrystallization to obtain 4.6 g(yield: 57%) of P-41.

Synthesis Example of P-91

In a round bottom flask, Core 1 (5 g, 14 mmol), Sub 9 (5.8 g, 15.4mmol), Pd(PPh₃)₄ (0.5 g, 0.4 mmol), K₂CO₃ (5.8 g, 41.9 mmol), THE andwater were added and stirred at 90° C. When the reaction was complete,the reaction mixture was extracted with CH₂Cl₂ and water. The organiclayer was dried over MgSO₄ and concentrated. The resulting compound wasseparated by silicagel column chromatography and recrystallization toobtain 4.7 g (yield: 51%) of P-91.

Synthesis Example of P-106

In a round bottom flask, Core 1 (5 g, 14 mmol), Sub 16 (5.8 g, 15.4mmol), Pd(PPh₃)₄ (0.5 g, 0.4 mmol), K₂CO₃ (5.8 g, 41.9 mmol), THE andwater were added and stirred at 90° C. When the reaction was complete,the reaction mixture was extracted with CH₂Cl₂ and water. The organiclayer was dried over MgSO₄ and concentrated. The resulting compound wasseparated by silicagel column chromatography and recrystallization toobtain 5.8 g (yield: 63%) of P-106.

Synthesis Example of P-146

In a round bottom flask, Core 11 (5 g, 14 mmol), Sub 2 (5.8 g, 15.4mmol), Pd(PPh₃)₄ (0.5 g, 0.4 mmol), K₂CO₃ (5.8 g, 41.9 mmol), THE andwater were added and stirred at 90° C. When the reaction was complete,the reaction mixture was extracted with CH₂Cl₂ and water. The organiclayer was dried over MgSO₄ and concentrated. The resulting compound wasseparated by silicagel column chromatography and recrystallization toobtain 4.7 g (yield: 51%) of P-146.

Synthesis Example of P-4

In a round bottom flask, Core 1 (5 g, 14 mmol), Sub 6 (5.9 g, 15.4mmol), Pd(PPh₃)₄ (0.5 g, 0.4 mmol), K₂CO₃ (5.8 g, 41.9 mmol), THE andwater were added and stirred at 90° C. When the reaction was complete,the reaction mixture was extracted with CH₂Cl₂ and water. The organiclayer was dried over MgSO₄ and concentrated. The resulting compound wasseparated by silicagel column chromatography and recrystallization toobtain 6.1 g (yield: 66%) of P-4. [Table 3] shows FD-MS (FieldDesorption-Mass Spectrometry) values of some compounds belonging toProduct.

TABLE 3 compound FD-MS P-1  m/z = 581.16 (C₃₉H₂₃N₃OS = 581.69) P-2  m/z= 631.17 (C₄₃H₂₅N₃OS = 631.75) P-3  m/z = 631.17 (C₄₃H₂₅N₃OS = 631.75)P-4  m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-5  m/z = 681.19 (C₄₇H₂₇N₃OS =681.81) P-6  m/z = 631.17 (C₄₃H₂₅N₃OS = 631.75) P-7  m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) P-8  m/z = 657.19 (C₄₅H₂₇N3OS = 657.79) P-9  m/z =657.19 (C₄₅H₂₇N₃OS = 657.79) P-10  m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79)P-11  m/z = 586.19 (C₃₉H₁₈D₅N₃OS = 586.72) P-12  m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) P-13  m/z = 681.19 (C₄₇H₂₇N₃OS = 681.81) P-14  m/z= 707.20 (C₄₉H₂₉N₃OS = 707.85) P-15  m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85)P-16  m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-17  m/z = 636.20(C₄₃H₂₀D₅N₃OS = 636.78) P-18  m/z = 681.19 (C₄₇H₂₇N₃OS = 681.81) P-19 m/z = 681.19 (C₄₇H₂₇N₃OS = 681.81) P-20  m/z = 707.20 (C₄₉H₂₉N₃OS =707.85) P-21  m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-22  m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-23  m/z = 636.20 (C₄₃H₂₀D₅N₃OS = 636.78) P-24 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-25  m/z = 707.20 (C₄₉H₂₉N₃OS =707.85) P-26  m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-27  m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-28  m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-29  m/z= 662.22 (C₄₅H₂₂D₅N₃OS = 662.82) P-30  m/z = 662.22 (C₄₅H₂₂D₅N₃OS =662.82) P-31  m/z = 581.16 (C₃₉H₂₃N₃OS = 581.69) P-32  m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) P-33  m/z = 631.17 (C₄₃H₂₅N₃OS = 631.75) P-34  m/z= 657.19 (C₄₅H₂₇N₃OS = 657.79) P-35  m/z = 681.19 (C₄₇H₂₇N₃OS = 681.81)P-36  m/z = 631.17 (C₄₃H₂₅N₃OS = 631.75) P-37  m/z = 631.17 (C₄₃H₂₅N₃OS= 631.75) P-38  m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-39  m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) P-40  m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-41  m/z= 586.19 (C₃₉H₁₈D₅N₃OS = 586.72) P-42  m/z = 681.19 (C₄₇H₂₇N₃OS =681.81) P-43  m/z = 681.19 (C₄₇H₂₇N₃OS = 681.81) P-44  m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-45  m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-46  m/z= 707.20 (C₄₉H₂₉N₃OS = 707.85) P-47  m/z = 636.20 (C₄3H₂₀D₅N₃OS =636.78) P-48  m/z = 681.19 (C₄₇H₂₇N₃OS = 681.81) P-49  m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) P-50  m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-51  m/z= 707.20 (C₄₉H₂₉N₃OS = 707.85) P-52  m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85)P-53  m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-54  m/z = 707.20 (C₄₉H₂₉N₃OS= 707.85) P-55  m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-56  m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-57  m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-58  m/z= 733.22 (C₅₁H₃₁N₃OS = 733.89) P-59  m/z = 662.22 (C₄₅H₂₂DN₃OS = 662.82)P-60  m/z = 662.22 (C₄₅H₂₂DN₃OS = 662.82) P-61  m/z = 657.19 (C₄₅H₂₇N₃OS= 657.79) P-62  m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-63  m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-64  m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-65  m/z= 757.22 (C₅₃H₃₁N₃OS = 757.91) P-66  m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85)P-67  m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-68  m/z = 733.22 (C₅₁H₃₁N₃OS= 733.89) P-69  m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-70  m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-71  m/z = 662.22 (C₄₅H₂₂D₅N₃OS = 662.82) P-72 m/z = 757.22 (C₅₃H₃₁N₃OS = 757.91) P-73  m/z = 757.22 (C₅₃H₃₁N₃OS =757.91) P-74  m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-75  m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-76  m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-77  m/z= 71 2.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-78  m/z = 757.22 (C₅₃H₃₁N₃OS =757.91) P-79  m/z = 757.22 (C₅₃H₃₁N₃OS = 757.91) P-80  m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-81  m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-82  m/z= 783.23 (C₅₅H₃₃N₃OS = 783.95) P-83  m/z = 712.23 (C₄₉H₂₄D₅N₃OS =712.88) P-84  m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-85  m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-86  m/z = 809.25 (C₅₇H₃₅N₃OS = 809.99) P-87  m/z= 809.25 (C₅₇H₃₅N₃OS = 809.99) P-88  m/z = 809.25 (C₅₇H₃₅N₃OS = 809.99)P-89  m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-90  m/z = 738.25(C₅₁H₂₆D₅N₃OS = 738.92) P-91  m/z = 662.22 (C₄₅H₂₂DN₃OS = 662.82) P-92 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-93  m/z = 712.23 (C₄₉H₂₄D₅N₃OS =712.88) P-94  m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-95  m/z = 762.25(C₅₃H₂₆D₅N₃OS = 762.94) P-96  m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-97 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-98  m/z = 738.25 (C₅₁H₂₆D₅N₃OS =738.92) P-99  m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-100 m/z = 738.25(C₅₁H₂₆D₅N₃OS = 738.92) P-101 m/z = 667.25 (C₄₅H₁₇D₁₀N₃OS = 667.85)P-102 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-103 m/z = 707.20 (C₄₉H₂₉N₃OS= 707.85) P-104 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-105 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-106 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-107 m/z= 707.20 (C₄₉H₂₉N₃OS = 707.85) P-108 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85)P-109 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-110 m/z = 757.22 (C₅₃H₃₁N₃OS= 757.91) P-111 m/z = 707.20 (C₄₉H₂₉N₃OS = 707.85) P-112 m/z = 707.20(C₄₉H₂₉N₃OS = 707.85) P-113 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P-114 m/z= 733.22 (C₅₁H₃₁N₃OS = 733.89) P-115 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89)P-116 m/z = 662.22 (C₄₅H₂₂D₅N₃OS = 662.82) P-117 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) P-118 m/z = 757.22 (C₅₃H₃₁N₃OS = 757.91) P-119 m/z= 783.23 (C₅₅H₃₃N₃OS = 783.95) P-120 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95)P-121 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-122 m/z = 712.23(C₄₉H₂₄D₅N₃OS = 712.88) P-123 m/z = 757.22 (C₅₃H₃₁N₃OS = 757.91) P-124m/z = 757.22 (C₅₃H₃₁N₃OS = 757.91) P-125 m/z = 783.23 (C₅₅H₃₃N₃OS =783.95) P-126 m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-127 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-128 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-129m/z = 783.23 (C₅₅H₃₃N₃OS = 783.95) P-130 m/z = 783.23 (C₅₅H₃₃N₃OS =783.95) P-131 m/z = 809.25 (C₅₇H₃₅N₃OS = 809.99) P-132 m/z = 809.25(C₅₇H₃₅N₃OS = 809.99) P-133 m/z = 809.25 (C₅₇H₃₅N₃OS = 809.99) P-134 m/z= 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-135 m/z = 738.25 (C₅₁H₂₆D₅N₃OS =738.92) P-136 m/z = 662.22 (C₄₅H₂₂D₅N₃OS = 662.82) P-137 m/z = 712.23(C₄₉H₂₄D₅N₃OS = 712.88) P-138 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-139m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-140 m/z = 762.25 (C₅₃H₂₆D₅N₃OS =762.94) P-141 m/z = 712.23 (C₄₉H₂₄D₅N₃OS = 712.88) P-142 m/z = 712.23(C₄₉H₂₄D₅N₃OS = 712.88) P-143 m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-144m/z = 738.25 (C₅₁H₂₆D₅N₃OS = 738.92) P-145 m/z = 738.25 (C₅₁H₂₆D₅N₃OS =738.92) P-146 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-147 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-148 m/z = 662.22 (C₄₅H₂₂D₅N₃OS = 662.82) P-149m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-150 m/z = 662.22 (C₄₅H₂₂D₅N₃OS =662.82) P-151 m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) P-152 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) P-153 m/z = 662.22 (C₄₅H₂₂D₅N₃OS = 662.82) p-154m/z = 657.19 (C₄₅H₂₇N₃OS = 657.79) p-155 m/z = 657.19 (C₄₅H₂₇N₃OS =657.79) P-156 m/z = 631.17 (C₄₃H₂₅N₃OS = 631.75) P-157 m/z = 681.19(C₄₅H₂₇N₃OS = 681.81) p-158 m/z = 681.19 (C₄₅H₂₇N₃OS = 681.81) P-159 m/z= 707.20 (C₄₉H₂₉N₃OS = 707.85) p-160 m/z = 781.22 (C₅₅H₃₁N₃OS = 781.93)

Synthesis Example 2

The compounds (final products 2) represented by Formula (12) accordingto the present invention can be prepared by reacting Sub 3-1 and Sub 3-2as shown in the following Reaction Scheme 4, but are not limitedthereto.

Synthesis Example of 4-1

3-bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol) was dissolved in THF, and(9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazol-3-yl)boronic acid (8.8g, 20 mmol), Pd(PPh₃)₄ (0.03 eq.), K₂CO₃ (3 eq.) and water were addedand refluxed with stirring. After the reaction was completed, thereaction mixture was extracted with ether and water. The organic layerwas dried over MgSO₄ and concentrated. The resulting organic materialwas separated by silicagel column chromatography and recrystallizationto obtain 9.2 g (yield: 72%) of the product.

Synthesis Example of 4-21

10-bromo-7-(pyridin-2-yl)-7H-benzo[c]carbazole (7.5 g, 2 mmol),dibenzo[b,d]furan-2-ylboronic acid (4.2 g, 20 mmol) were carried out inthe same manner as 4-1 to obtain 6.5 g of the product (yield: 71%)

Synthesis Example of 4-25

9-([1,1′-biphenyl]-4-yl)-3-bromo-9H-carbazole (8.0 g, 20 mmol),(9-(naphthalen-2-yl)-9H-carbazol-3-yl)boronic acid (6.7 g, 20 mmol) werecarried out in the same manner as 4-1 to obtain 9.2 g of the product(yield: 75%)

Synthesis Example of 4-31

3′-bromo-9-phenyl-9H-2,9′-bicarbazole (9.7 g, 20 mmol),(9-phenyl-9H-carbazol-3-yl)boronic acid (5.7 g, 20 mmol) were carriedout in the same manner as 4-1 to obtain 9.5 g of the product (yield:73%)

Synthesis Example of 4-32

3-bromo-9-(dibenzo[b,d]furan-2-yl)-9H-carbazole (8.2 g, 20 mmol),(12-([1,1′:4′,1″-terphenyl]-4-yl)-12H-benzo[4,5]thieno[2,3-a]carbazol-3-yl)boronicacid (10.9 g, 20 mmol) were carried out in the same manner as 4-1 toobtain 11.5 g of the product (yield: 69%)

Synthesis Example of 4-34

4-bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol),(4-(dibenzo[b,d]thiophen-3-yl)phenyl)boronic acid (6.1 g, 20 mmol) werecarried out in the same manner as 4-1 to obtain 6.7 g of the product(yield: 67%)

Synthesis Example of 4-35

3-bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol),9(9,9-dimethyl-9H-fluoren-3-yl)boronic acid (4.8 g, 20 mmol) werecarried out in the same manner as 4-1 to obtain 6.1 g of the product(yield: 70%)

TABLE 4 compound FD-MS 4-1  m/z = 639.24 (C₄₅H₂₉N₅ = 639.75) 4-2  m/z =715.27 (C₅₁H₃₃N₅ = 715.84) 4-3  m/z = 780.33 (C₅₇H₄₀N₄ = 780.95) 4-4 m/z = 639.24 (C₄₅H₂₉N₅ = 639.75) 4-5  m/z = 715.27 (C₅₁H₃₃N₅ = 715.84)4-6  m/z = 780.33 (C₅₇H₄₀N₄ = 780.95) 4-7  m/z = 612.23 (C₄₄H₂₆N₄ =612.72) 4-8  m/z = 612.23 (C₄₄H₂₆N₄ = 612.72) 4-9  m/z = 662.25(C₄₆H₃₀N₄ = 662.78) 4-10 m/z = 484.19 (C₃₆H₂₄N₂ = 484.59) 4-11 m/z =639.24 (C₄₅H₂₉N₅ = 639.75) 4-12 m/z = 715.27 (C₅₁H₃₃N₅ = 715.84) 4-13m/z = 715.27 (C₅₁H₃₃N₅ = 715.84) 4-14 m/z = 638.25 (C₄₆H₃₀N₄ = 638.76)4-15 m/z = 579.18 (C₄₀H₂₅N₃S = 579.71) 4-16 m/z = 410.14 (C₂₉H₁₆N₂S =410.47) 4-17 m/z = 486.17 (C₃₅H₂₂N₂O = 486.56) 4-18 m/z = 486.17(C₃₅H₂₂N₂O = 486.56) 4-19 m/z = 486.17 (C₃₅H₂₂N₂O = 486.56) 4-20 m/z =563.20 (C₄₀H₂₅N₃O = 563.65) 4-21 m/z = 460.16 (C₃₃H₂₀N₂O = 460.52) 4-22m/z = 536.19 (C₃₉H₂₄N₂O = 536.62) 4-23 m/z = 689.26 (C₄₉H₃₁N₅ = 689.80)4-24 m/z = 585.22 (C₄₃H₂₇N₃ = 585.69) 4-25 m/z = 610.24 (C₄₆H₃₀N₂ =610.76) 4-26 m/z = 610.24 (C₄₆H₃₀N₂ = 610.76) 4-27 m/z = 636.26(C₄₆H₃₂N₂ = 636.80) 4-28 m/z = 636.26 (C₄₆H₃₂N₂ = 636.80) 4-29 m/z =610.24 (C₄₆H₃₀N₂ = 610.76) 4-30 m/z = 610.24 (C₄₆H₃₀N₂ = 610.76) 4-31m/z = 649.25 (C₄₆H₃₁N₃ = 649.80) 4-32 m/z = 832.25 (C₆₀H₃₆N₂OS = 833.02)4-33 m/z = 560.23 (C₄₂H₂₆N₂ = 560.70) 4-34 m/z = 501.16 (C₃₆H₂₃NS =501.65) 4-35 m/z = 435.20 (C₃₃H₂₅N = 435.57) 4-36 m/z = 725.28 (C₅₄H₃₅N₃= 725.90) 4-37 m/z = 650.24 (C₄₈H₃₀N₂O = 650.78) 4-38 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 4-39 m/z = 650.24 (C₄₈H₃₀N₂O = 650.78) 4-40 m/z =650.24 (C₄₈H₃₀N₂O = 650.78) 4-41 m/z = 666.21 (C₄₈H₃₀N₂S = 666.84) 4-42m/z = 666.21 (C₄₈H₃₀N₂S = 666.84) 4-43 m/z = 666.21 (C₄₈H₃₀N₂S = 666.84)4-44 m/z = 666.21 (C₄₈H₃₀N₂S = 666.84) 4-45 m/z = 650.24 (C₄₈H₃₀N₂O =650.78) 4-46 m/z = 650.24 (C₄₈H₃₀N₂O = 650.78) 4-47 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 4-48 m/z = 650.24 (C₄₈H₃₀N₂O = 650.78) 4-49 m/z =666.21 (C₄₈H₃₀N₂S = 666.84) 4-50 m/z = 666.21 (C₄₈H₃₀N₂S = 666.84) 4-51m/z = 666.21 (C₄₈H₃₀N₂S = 666.84) 4-52 m/z = 666.21 (C₄₈H₃₀N₂S = 666.84)

Synthesis Example 3

Final products represented by Formula (18) according to the presentinvention can be prepared by reacting as follows, but are not limitedthereto.

Synthesis Example of 13-17

9-(4′-bromo-[1,1′-biphenyl]-4-yl)-9H-carbazole (9.6 g, 24 mmol) wasdissolved in toluene, and di([1,1′-biphenyl]-4-yl)amine (6.4 g, 20mmol), Pd₂(dba)₃ (0.05 eq.), PPh₃ (0.1 eq.), NaOt-Bu (3 eq.) were addedand refluxed with stirring at 100° C. at 24 hours. After the reactionwas completed, the reaction mixture was extracted with ether and water.The organic layer was dried over MgSO₄ and concentrated. The resultingorganic material was separated by silicagel column chromatography andrecrystallization to obtain 12.9 g (yield: 84%) of the product.

Synthesis Example of 13-32

3-(4-bromophenyl)-9-phenyl-9H-carbazole (9.6 g, 24 mmol) was dissolvedin toluene, and N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine(7.2 g, 20 mmol), Pd₂(dba)₃ (0.05 eq.), PPh₃ (0.1 eq.), NaOt-Bu (3 eq.)were added and refluxed with stirring at 100° C. at 24 hours. After thereaction was completed, the reaction mixture was extracted with etherand water. The organic layer was dried over MgSO₄ and concentrated. Theresulting organic material was separated by silicagel columnchromatography and recrystallization to obtain 13.8 g (yield: 85%) ofthe product.

Synthesis Example of 2-34

In a round bottom flask, Sub 4(19) (9.5 g, 20 mmol), Sub 5(4) (4.7 g, 20mmol), Pd₂(dba)₃ (0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa(5.8 g, 60 mmol), toluene (300 mL) were added and were carried out at100° C. When the reaction was complete, the reaction mixture wasextracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄and concentrated. The resulting compound was separated by silicagelcolumn chromatography and recrystallization to obtain 9.8 g (yield: 78%)of 2-34.

Synthesis EXAMPLE of 2-58

In a round bottom flask, Sub 4(35) (8.4 g, 20 mmol), Sub 5(7) (5.7 g, 20mmol), Pd₂(dba)₃ (0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa(5.8 g, 60 mmol) and toluene (300 mL) were carried out in the samemanner as in 2-34 to give 2-58. (10.4 g, 83%).

Synthesis Example of 2-59

In a round bottom flask, Sub 4(32) (12.9 g, 20 mmol), Sub 5(11) (7.9 g,20 mmol), Pd₂(dba)₃ (0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa(5.8 g, 60 mmol) and toluene (300 mL) were carried out in the samemanner as in 2-34 to give 2-59. (5.2 g, 79%).

Synthesis Example of 2-69

In a round bottom flask,N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (7.2 g, 20mmol), 4-(2-bromophenyl)-9,9-diphenyl-9H-fluorene (9.5 g, 20 mmol),Pd₂(dba)₃ (0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g,60 mmol) and toluene (300 mL) were carried out in the same manner as in2-34 to give 2-69. (12.2 g, 81%).

Synthesis Example of 2-71

In a round bottom flask,N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine (7.5 g, 20mmol),N-(3-bromophenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine(10.6 g, 20 mmol), Pd₂(dba)₃ (0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were carried out inthe same manner as in 2-34 to give 2-71. (12.9 g, 78%).

Synthesis Example 4

Final products represented by Formula (30) according to the presentinvention can be prepared by reacting Sub 30 and Sub 31 as shown inReaction Scheme 5 below, but are not limited thereto.

Synthesis Example of Sub 30

Synthesis Example of Sub 30(81)

In a round bottom flask, 3-(9-phenyl-9H-fluoren-9-yl)aniline (6.7 g, 20mmol), 2-bromo-9,9-dimethyl-9H-fluorene (5.5 g, 20 mmol), Pd₂(dba)₃ (0.5g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) andtoluene (300 mL) were carried out in the same manner as in 2-34 to giveSub 30(81). (8.83 g, 84%).

Examples of Sub 31

Examples of Sub 31 are as follows, but are not limited thereto.

TABLE 5 compound FD-MS Sub m/z = 155.96 (C₆H₅Br = 157.01) 31-1  Sub m/z= 205.97 (C₁₀H₇Br = 207.07) 31-2  Sub m/z = 205.97 (C₁₀H₇Br = 207.07)31-3  Sub m/z = 231.99 (C₁₂H₉Br = 233.10) 31-4  Sub m/z = 309.02(C₁₇H₁₂BrN = 310.19) 31-5  Sub m/z = 311.01 (C₁₅H₁₀BrN₃ = 312.16) 31-6 Sub m/z = 310.01 (C₁₆H₁₁BrN₂ = 311.18) 31-7  Sub m/z = 310.01(C₁₆H₁₁BrN₂ = 311.18) 31-8  Sub m/z = 310.01 (C₁₆H₁₁BrN₂ = 311.18) 31-9 Sub m/z = 387.04 (C₂₁H₁₄BrN₃ = 388.26) 31-10 Sub m/z = 386.04(C₂₂H₁₅BrN₂ = 387.27) 31-11 Sub m/z = 386.04 (C₂₂H₁₅BrN₂ = 387.27) 31-12Sub m/z = 348.03 (C₁₉H₁₃BrN₂ = 349.22) 31-13 Sub m/z = 271.99 (C₁₃H₉BrN₂= 273.13) 31-14 Sub m/z = 283.99 (C₁₄H₉BrN₂ = 285.14) 31-15 Sub m/z =374.01 (C₂₀H₁₁BrN₂O = 375.22) 31-16 Sub m/z = 400.06 (C₂₃H₁₇BrN₂ =401.30) 31-17 Sub m/z = 360.03 (C₂₀H₁₃BrN₂ = 361.23) 31-18 Sub m/z =476.09 (C₂₉H₂₁BrN₂ = 477.39) 31-19

Synthesis Example of 2-72

In a round bottom flask,N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)dibenzo[b,d]furan-1-amine (10.0 g,20 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (5.5 g, 20 mmol), Pd₂(dba)₃(0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol)and toluene (300 mL) were carried out in the same manner as in 2-34 togive 2-72. (11.1 g, 80%).

Synthesis Example of 2-81

In a round bottom flask, Sub 30(81) (10.3 g, 20 mmol), Sub 31-4 (4.66 g,20 mmol), Pd₂(dba)₃ (0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa(5.8 g, 60 mmol) and toluene (300 mL) were carried out in the samemanner as in 2-34 to give 2-81. (10.3 g, 76%).

TABLE 6 Compound FD-MS 2-81  m/z = 677.31 (C₅₂H₃₉N = 677.89) 2-82  m/z =651.26 (C₄₉H₃₃NO = 651.81) 2-83  m/z = 641.22 (C₄₇H₃₁NS = 641.83) 2-84 m/z = 700.29 (C₅₃H₃₆N₂ = 700.89) 2-85  m/z = 677.31 (C₅₂H₃₉N = 677.89)2-86  m/z = 651.26 (C₄₉H₃₃NO = 651.81) 2-87  m/z = 843.30 (C₆₃H₄₁NS =844.09) 2-88  m/z = 701.28 (C₅₂H₃₅N₃ = 701.87) 2-89  m/z = 677.31(C₅₂H₃₉N = 677.89) 2-90  m/z = 729.28 (C₅₃H₃₅N₃O = 729.88) 2-91  m/z =912.29 (C₆₄H₄₀N₄₀S = 913.11) 2-92  m/z = 878.34 (C₆₅H₄₂N₄ = 879.08)2-93  m/z = 805.35 (C₆₀H₄₃N₃ = 806.03) 2-94  m/z = 906.34 (C₆₆H₄₂N₄O =907.09) 2-95  m/z = 769.26 (C₅₅H₃₅N₃S = 769.97) 2-96  m/z = 884.30(C₆₃H₄₀N₄S = 885.10) 2-97  m/z = 767.36 (C₅₉H₄₅N = 768.02) 2-98  m/z =815.32 (C₆₂H₄₁NO = 816.02) 2-99  m/z = 829.28 (C₆₂H₃₉NS = 830.06) 2-100m/z = 781.35 (C₅₉H₃₅D₅N₂ = 782.01) 2-101 m/z = 695.30 (C₅₂H₃₈FN =695.88) 2-102 m/z = 753.34 (C₅₈H₄₃N = 753.99) 2-103 m/z = 803.36(C₆₂H₄₅N = 804.05) 2-104 m/z = 6829.37 (C₆₄H₄₇N = 830.09) 2-105 m/z =918.40 (C₇₀H₅₀N₂ = 919.18) 2-106 m/z = 601.28 (C₄₆H₃₅N = 601.79) 2-107m/z = 677.31 (C₅₂H₃₉N = 677.89) 2-108 m/z = 753.34 (C₅₈H₄₃N = 753.99)2-109 m/z = 701.31 (C₅₄H₃₉N = 701.91) 2-110 m/z = 677.31 (C₅₂H₃₉N =677.89) 2-111 m/z = 677.31 (C₅₂H₃₉N = 677.89) 2-112 m/z = 682.34(C₅₂H₃₄D₅N = 682.92) 2-113 m/z = 701.31 (C₅₄H₃₉N = 701.91) 2-114 m/z =619.27 (C₄₆H₃₄FN = 619.78) 2-115 m/z = 753.34 (C₅₈H₄₃N = 753.99) 2-116m/z = 803.36 (C₆₂H₄₅N = 804.05) 2-117 m/z = 701.31 (C₅₄H₃₉N = 701.91)2-118 m/z = 651.29 (C₅₀H₃₇N = 651.85) 2-119 m/z = 727.32 (C₅₆H₄₁N =727.95) 2-120 m/z = 758.37 (C₅₈H₃₈D₅N = 759.02) 2-121 m/z = 757.37(C₅₈H₄₇N = 758.02) 2-122 m/z = 753.34 (C₅₈H₄₃N = 753.99) 2-123 m/z =803.36 (C₆₂H₄₅N = 804.05) 2-124 m/z = 834.40 (C₆₄H₄₂D₅N = 835.12) 2-125m/z = 883.33 (C₆₆H₄₅NS = 884.15) 2-126 m/z = 651.26 (C₄₉H₃₃NO = 651.81)2-127 m/z = 641.22 (C₄₇H₃₁NS = 641.83) 2-128 m/z = 700.29 (C₅₃H₃₆N₂ =700.89) 2-129 m/z = 677.31 (C₅₂H₃₉N = 677.89) 2-130 m/z = 651.26(C₄₉H₃₃NO = 651.81) 2-131 m/z = 843.30 (C₆₃H₄₁NS = 844.09) 2-132 m/z =701.28 (C₅₂H₃₅N₃ = 701.87) 2-133 m/z = 677.31 (C₅₂H₃₉N = 677.89) 2-134m/z = 729.28 (C₅₃H₃₅N₃O = 729.88) 2-135 m/z = 912.29 (C₆₄H₄₀N₄OS =913.11) 2-136 m/z = 878.34 (C₆₅H₄₂N₄ = 879.08) 2-137 m/z = 805.35(C₆₀H₄₃N₃ = 806.03) 2-138 m/z = 906.34 (C₆₆H₄₂N₄O = 907.09) 2-139 m/z =769.26 (C₅₅H₃₅N₃S = 769.97) 2-140 m/z = 884.30 (C₆₃H₄₀N₄S = 885.10)2-141 m/z = 767.36 (C₅₉H₄₅N = 768.02) 2-142 m/z = 815.32 (C₆₂H₄₁NO =816.02) 2-143 m/z = 829.28 (C₆₂H₃₉NS = 830.06) 2-144 m/z = 781.35(C₅₉H₃₅D₅N₂ = 782.01) 2-145 m/z = 695.30 (C₅₂H₃₈FN = 695.88) 2-146 m/z =753.34 (C₅₈H₄₃N = 753.99) 2-147 m/z = 803.36 (C₈₂H₄₅N = 804.05) 2-148m/z = 6829.37 (C₈₄H₄₇N = 830.09) 2-149 m/z = 918.40 (C₇₀H₅₀N₂ = 919.18)2-150 m/z = 717.34 (C₅₅H₄₃N = 717.96) 2-151 m/z = 717.34 (C₅₅H₄₃N =717.96) 2-152 m/z = 717.34 (C₅₅H₄₃N = 717.96) 2-153 m/z = 717.34(C₅₅H₄₃N = 717.96)

Evaluation of Manufacture of Organic Electronic Element Example 1)Manufacture and Evaluation of Green Organic Light Emitting Diode (Host)

First, on an ITO layer (anode) formed on a glass substrate,N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine (hereinafter will be abbreviated as 2-TNATA) wasvacuum-deposited to form a hole injection layer with a thickness of 60nm, and on the layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl(hereinafter will be abbreviatedas NPD) was vacuum-deposited as hole transport compounds to form a holetransport layer with a thickness of 60 nm. Subsequently, the inventivecompound represented by Formula (1) was used as a host, and an emittinglayer with a thickness of 30 nm was deposited as a dopant on the holetransport layer by doping Ir(ppy)3[tris(2-phenylpyridine)-iridium] witha weight of 95:5.(1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter abbreviated as BAIq) was vacuum deposited as a holeblocking layer to a thickness of 10 nm, and Tris(8-quinolinol) aluminum(hereinafter abbreviated as Alq3) was deposited as an electron transportlayer to a thickness of 40 nm. After that, an alkali metal halide, LiFwas vacuum deposited as an electron injection layer to a thickness of0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathodeto manufacture an OLED.

To the OLEDs which were manufactured by examples and comparativeexamples, a forward bias direct current voltage was applied, andelectroluminescent (EL) properties were measured using PR-650 ofPhotoresearch Co., and T95 life was measured using a life measuringapparatus manufactured by McScience Inc. with a reference luminance of5000 cd/m². In the following table, the manufacture of a device and theresults of evaluation are shown.

Comparative Examples 1˜4

An OLED was prepared in the same manner as in Example 1, except thatComparative Compound A, Comparative Compound B, Comparative Compound Cand Comparative Compound D were used as a host.

TABLE 7 Current Density Brightness Efficiency CIE compound Voltage(mA/cm²) (cd/m²) (cd/A) T (95) x y comparative comparative 5.9 24.95000.0 20.1 66.1 0.33 0.61 example (1) compound A comparativecomparative 5.6 19.4 5000.0 25.8 71.3 0.32 0.63 example (2) compound Bcomparative comparative 5.7 23.1 5000.0 21.6 75.7 0.31 0.64 example (3)compound C comparative comparative 5.5 16.8 5000.0 29.7 80.1 0.30 0.61example (4) compound D example (1) P-8  5.3 13.8 5000.0 36.1 91.5 0.340.62 example (2) P-29  5.0 13.5 5000.0 37.1 98.5 0.34 0.61 example (3)P-32  5.4 13.8 5000.0 36.3 87.6 0.30 0.64 example (4) P-61  5.1 12.75000.0 39.4 94.6 0.31 0.61 example (5) P-91  5.0 12.6 5000.0 39.6 93.30.33 0.63 example (6) P-146 5.1 12.5 5000.0 39.9 94.3 0.35 0.60 example(7) P-154 5.1 12.6 5000.0 39.6 94.2 0.33 0.64 example (8) P-156 5.2 13.65000.0 36.7 93.0 0.31 0.60

Example 2) Manufacture and Evaluation of Green Organic Light EmittingDiode (Mixed Host)

First, on an ITO layer (anode) formed on a glass substrate,N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N-phenylbenzene-1,4-diamine (hereinafter will be abbreviated as 2-TNATA) wasvacuum-deposited to form a hole injection layer with a thickness of 60nm, and on the layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl(hereinafter will be abbreviatedas NPD) was vacuum-deposited as hole transport compounds to form a holetransport layer with a thickness of 60 nm. Subsequently, a mixture ofthe inventive compound represented by Formula (1) and the compoundrepresented by Formula (12) in a ratio of 6:4 was used as a host, and asa dopant, an emitting layer with a thickness of 30 nm was deposited onthe hole transport layer by dopingIr(ppy)3[tris(2-phenylpyridine)-iridium] with a weight of 95:5.(1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter abbreviated as BAIq) was vacuum deposited as a holeblocking layer to a thickness of 10 nm, and Tris(8-quinolinol) aluminum(hereinafter abbreviated as Alq3) was deposited as an electron transportlayer to a thickness of 40 nm. After that, an alkali metal halide, LiFwas vacuum deposited as an electron injection layer to a thickness of0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathodeto manufacture an OLED.

To the OLEDs which were manufactured by examples and comparativeexamples, a forward bias direct current voltage was applied, andelectroluminescent (EL) properties were measured using PR-650 ofPhotoresearch Co., and T95 life was measured using a life measuringapparatus manufactured by McScience Inc. with a reference luminance of5000 cd/m². In the following table, the manufacture of a device and theresults of evaluation are shown.

Comparative Examples 5˜8, 10˜13

An OLED was prepared in the same manner as in Example 2, except thatComparative Compound A, Comparative Compound B, Comparative Compound C,and Comparative Compound D were used as a host instead of the inventivecompound represented by Formula (1).

Comparative Example 9 and 14

An OLED was prepared in the same manner as in Example 2, except forusing the comparative compound E instead of the inventive compoundrepresented by Formula (12) as a host,

TABLE 8 First Second Current Brightnes Lifetime host host VoltageDensity (cd/m²) Efficiency T (95) comparative comparative 4-27 5.3 21.45000.0 23.4 120.4 example (5) compound A comparative comparative 5.217.3 5000.0 28.9 124.8 example (6) compound B comparative comparative5.1 19.9 5000.0 25.1 129.6 example (7) compound C comparativecomparative 5.0 15.0 5000.0 33.3 133.2 example (8) compound Dcomparative comparative 5.0 12.9 5000.0 38.8 110.1 example (9) compoundE comparative comparative 4-31 5.2 22.0 5000.0 22.7 109.8 example (10)compound A comparative comparative 5.0 17.7 5000.0 28.2 115.4 example(11) compound B comparative comparative 4.8 20.2 5000.0 24.8 119.1example (12) compound C comparative comparative 4.7 16.2 5000.0 30.9123.3 example (13) compound D comparative comparative 5.3 13.2 5000.037.9 101.7 example (14) compound E example (9)  P-8  4-27 4.7 12.25000.0 41.0 133.7 example (10) P-29  4.4 11.1 5000.0 45.2 142.8 example(11) P-32  4.8 12.3 5000.0 40.6 130.1 example (12) P-61  4.5 11.8 5000.042.5 135.7 example (13) P-91  4.5 11.7 5000.0 42.8 135.3 example (14)P-146 4.5 11.9 5000.0 42.0 135.9 example (15) P-154 4.5 11.9 5000.0 42.1135.3 example (16) P-156 4.7 12.2 5000.0 40.9 131.4 example (17) P-8 4-31 4.2 12.2 5000.0 40.9 130.9 example (18) P-29  4.1 11.1 5000.0 45.0140.4 example (19) P-32  4.6 12.4 5000.0 40.4 128.2 example (20) P-61 4.3 11.8 5000.0 42.5 133.5 example (21) P-91  4.4 11.8 5000.0 42.4 130.1example (22) P-146 4.2 11.8 5000.0 42.3 132.4 example (23) P-154 4.411.9 5000.0 42.2 133.9 example (24) P-156 4.6 12.3 5000.0 40.6 129.7

Example 3) Manufacture and Evaluation of Green Organic Light EmittingDiode (Emitting Auxiliary Layer+Mixed Host)

First, on an ITO layer (anode) formed on a glass substrate,N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine(hereinafter will be abbreviated as 2-TNATA) was vacuum-deposited toform a hole injection layer with a thickness of 60 nm. Subsequently, onthe layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl(hereinafterwill be abbreviated as NPD) was vacuum-deposited as an hole transportcompound to a thickness of 60 nm to form a hole transport layer.Subsequently, the inventive compound represented by Formula (18) wasvacuum-deposited as an emitting auxiliary layer material to a thicknessof 20 nm to form an emitting auxiliary layer. After forming the emittingauxiliary layer, a mixture of the inventive compound represented byFormula (1) and the compound represented by Formula (12) in a ratio of6:4 was used on the emitting auxiliary layer, and as a dopant, anemitting layer with a thickness of 30 nm was deposited by dopingIr(ppy)3[tris(2-phenylpyridine)-iridium] with a weight of 95:5.(1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter abbreviated as BAIq) was vacuum deposited as a holeblocking layer to a thickness of 10 nm, and Tris(8-quinolinol) aluminum(hereinafter abbreviated as Alq3) was deposited as an electron transportlayer to a thickness of 40 nm. After that, an alkali metal halide, LiFwas vacuum deposited as an electron injection layer to a thickness of0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathodeto manufacture an OLED.

To the OLEDs which were manufactured by examples and comparativeexamples, a forward bias direct current voltage was applied, andelectroluminescent (EL) properties were measured using PR-650 ofPhotoresearch Co., and T95 life was measured using a life measuringapparatus manufactured by McScience Inc. with a reference luminance of5000 cd/m². In the following table, the manufacture of a device and theresults of evaluation are shown.

Comparative Examples 15˜29

An OLED was prepared in the same manner as in Example 3, except that thecomparative compound A to E are each used instead of the inventivecompound represented by Formula (1) as a host,

TABLE 9 Emitting auxiliary First Second Current Brightness Lifetimelayer host host Voltage Density (cd/m²) Efficiency T (95) comparative2-69 comparative 4-27 5.2 16.6  5000.0 30.1 125.1 example (15) compoundA comparative comparative 5.2 13.8  5000.0 36.2 130.1 example (16)compound B comparative comparative 5.0 16.2  5000.0 30.8 135.3 example(17) compound C comparative comparative 5.0 12.6  5000.0 39.7 138.4example (18) compound D comparative comparative 5.4 11.0  5000.0 45.4115.6 example (19) compound E example (25) P-8  4.6 9.8 5000.0 51.1140.4 example (26) P-29  4.3 9.0 5000.0 55.7 150.9 example (27) P-61 4.4 9.6 5000.0 52.2 144.5 example (28) P-146 4.4 9.7 5000.0 51.6 143.8comparative 2-72 comparative 5.1 14.1  5000.0 35.4 130.4 example (20)compound A comparative comparative 5.0 12.1  5000.0 41.3 135.9 example(21) compound B comparative comparative 4.9 13.9  5000.0 35.9 140.7example (22) compound C comparative comparative 5.0 11.4  5000.0 43.7143.1 example (23) compound D comparative comparative 5.3 10.6  5000.047.1 120.3 example (24) compound E example (29) P-8  4.4 8.3 5000.0 59.9145.9 example (30) P-29  4.0 7.7 5000.0 65.1 157.4 example (31) P-61 4.2 8.2 5000.0 60.7 150.1 example (32) P-146 4.3 8.2 5000.0 61.1 149.4comparative 2-74 comparative 5.0 13.9  5000.0 36.1 130.8 example (25)compound A comparative comparative 5.1 12.0  5000.0 41.7 136.1 example(26) compound B comparative comparative 4.8 14.2  5000.0 35.3 141.2example (27) compound C comparative comparative 4.9 11.5  5000.0 43.4143.7 example (28) compound D comparative comparative 5.1 9.8 5000.050.8 120.9 example (29) compound E example (33) P-8  4.3 8.5 5000.0 59.1146.2 example (34) P-29  3.9 7.7 5000.0 64.8 157.8 example (35) P-61 4.0 8.3 5000.0 60.3 150.6 example (36) P-146 4.1 8.2 5000.0 60.9 150.4comparative 2-82 comparative 4.9 10.4  5000.0 48.2 141.8 example (30)compound A comparative comparative 4.9 10.2  5000.0 48.8 142.4 example(31) compound B comparative comparative 4.8 10.3  5000.0 48.5 143.7example (32) compound C comparative comparative 4.9 10.0  5000.0 50.1145.3 example (33) compound D comparative comparative 4.9 9.9 5000.050.5 140.9 example (34) compound E example (37) P-8  3.7 8.0 5000.0 62.5160.8 example (38) P-29  3.7 7.6 5000.0 65.4 163.8 example (39) P-61 3.6 7.7 5000.0 64.8 163.2 example (40) P-146 3.6 8.0 5000.0 62.8 161.5

Example 4) Manufacture and Evaluation of Green Organic Light EmittingDiode (Hole Transport Layer+Emitting Auxiliary Layer+Mixed Host)

First, on an ITO layer (anode) formed on a glass substrate,N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine(hereinafter will be abbreviated as 2-TNATA) was vacuum-deposited toform a hole injection layer with a thickness of 60 nm. Subsequently, onthe layer, the compound represented by Formula (18) was vacuum-depositedto a thickness of 60 nm to form a hole transport layer. Subsequently,the compound represented by Formula (18) was vacuum-deposited as anemitting auxiliary material to a thickness of 20 nm to form an emittingauxiliary layer. After forming the emitting auxiliary layer, a mixtureof the inventive compound represented by Formula (1) and the compoundrepresented by Formula (12) in a ratio of 6:4 was used as a host, and asa dopant, an emitting layer with a thickness of 30 nm was deposited bydoping Ir(ppy)3[tris(2-phenylpyridine)-iridium] with a weight of 95:5.(1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter abbreviated as BAIq) was vacuum deposited as a holeblocking layer to a thickness of 10 nm, and Tris(8-quinolinol) aluminum(hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nmas an electron transport layer. After that, an alkali metal halide, LiFwas vacuum deposited as an electron injection layer to a thickness of0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathodeto manufacture an OLED.

To the OLEDs which were manufactured by examples and comparativeexamples, a forward bias direct current voltage was applied, andelectroluminescent (EL) properties were measured using PR-650 ofPhotoresearch Co., and T95 life was measured using a life measuringapparatus manufactured by McScience Inc. with a reference luminance of5000 cd/m². In the following table, the manufacture of a device and theresults of evaluation are shown.

TABLE 10 Hole Emitting transport auxiliary First Second CurrentBrightness Lifetime layer layer host host Voltage Density (cd/m²)Efficiency T (95) example (37) 13-32 2-72 P-8  4-27 4.2 7.8 5000.0 64.2149.1 example (38) P-29  3.9 7.1 5000.0 70.1 160.6 example (39) P-61 4.1 7.6 5000.0 65.9 155.8 example (40) P-146 4.2 7.6 5000.0 66.2 154.3example (41) 2-74 P-8  4.0 7.8 5000.0 63.8 151.4 example (42) P-29  3.87.2 5000.0 69.7 162.1 example (43) P-61  3.9 7.6 5000.0 65.4 155.8example (44) P-146 3.8 7.6 5000.0 66.0 155.7 example (45) 2-72 P-8  4.27.8 5000.0 64.2 149.1 example (46) P-29  3.9 7.1 5000.0 70.1 160.6example (47) P-61  4.1 7.6 5000.0 65.9 155.8 example (48) P-146 4.2 7.65000.0 66.2 154.3 example (49) 2-74 P-8  4.0 7.8 5000.0 63.8 151.4example (50) P-29  3.8 7.2 5000.0 69.7 162.1 example (51) P-61  3.9 7.65000.0 65.4 155.8 example (52) P-146 3.8 7.6 5000.0 66.0 155.7 example(53) 2-82 P-8  3.4 7.3 5000.0 68.9 163.6 example (54) P-29  3.2 6.85000.0 73.4 168.7 example (55) P-61  3.3 7.1 5000.0 70.2 166.7 example(56) P-146 3.3 7.2 5000.0 69.3 165.4

As can be seen from the results of Table 7 to 10, the organic electronicelement using the organic electronic device material of the presentinvention as a phosphorescent host can remarkably improve the highluminous efficiency, the low driving voltage and the lifetime.

Table 7 shows the superiority of the compounds of the invention comparedto the comparative compounds when the inventive compound represented byFormula (1) was used as a single host. In the results of ComparativeCompound A and Comparative Compound C, when the 3-dibenzofuran wassubstituted, the performance was improved in all aspects of drivingvoltage, efficiency and lifetime, compared with 4-dibenzofuran. In theresults of Comparative Compound A and Comparative Compound B, orComparative Compound C and Comparative Compound D, it can be confirmedthat the performance of the triazine substituted with twodibenzothiophen or dibenzofuran moiety is improved compared with thetriazine substituted with one dibenzothiophen or dibenzofuran moiety.Thus, it can be finally confirmed that the inventive compound, in whichtriazine is substituted with 3-dibenzofuran and is linked by a linkerwith 4-dibenzothiophen to the other side, exhibits an improved resultwhich is significantly different from the comparative compounds A to D.It is suggested that the energy level (HOMO, LUMO, T1, etc.) of thecompound may vary significantly depending on the kind of the substituentor the substitution position, and the differences in the physicalproperties of compounds may act as key factors (ex. energy balance) inimproving device performance during device deposition, resulting indifferent device results.

Table 8 shows that when the compound represented by Formula (12) and thecompound of Formula (1) are mixed, they are significantly better thanother comparison combinations. This result is also supported theexplanations in the case of a single host, and when bonded to Formula(12), the driving and efficiency can be improved by about 24% and thelifetime can be improved by about 63% compared with a single host. Whentwo hosts are premixed, the aging rate is very important to deposit at acertain rate, and the compound of the present invention was superior inthe aging rate compared with other materials, and particularly, thecompound that at least one of Ar¹, Ar³ and R³ is a C₆-C₂₄ aryl group hasthe best results in the aging test.

Table 9 is the examples using the mixed compound of Formula (1) andFormula (12) as the emitting layer host and using the compoundrepresented by Formula (18) in the emitting auxiliary layer, and showsthat the efficiency is improved by about 60% and the lifetime isimproved by about 20% compared with Table 8. Here, using the compoundrepresented by Formula (18) as the hole transport compound also yieldedslightly improved results in terms of driving voltage, efficiency, andlifetime in comparison with the results in Table 7.

That is, the compound of the present invention exhibits improved resultscompared with the known compounds even when used as a single host, butwhen used in combination with the compound represented by Formula (12),or when the compound represented by Formula (18) was used for theemitting auxiliary layer or the hole transport layer, remarkable resultswere obtained.

Example 5) Manufacture and Evaluation of Blue Organic Light EmittingDiode

First, on an ITO layer (anode) formed on a glass substrate,N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine(hereinafter will be abbreviated as 2-TNATA) was vacuum-deposited toform a hole injection layer with a thickness of 60 nm. Subsequently, andon the layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl(hereinafterwill be abbreviated as NPD) was vacuum-deposited to a thickness of 60 nmto form a hole transport layer. Subsequently, the inventive compound wasvacuum-deposited as an emitting auxiliary layer material to a thicknessof 20 nm to form an emitting auxiliary layer. After forming the emittingauxiliary layer, on the emitting auxiliary layer,9,10-di(naphthalen-2-yl)anthracene is used as a host, and BD-052X(Idemitsu kosan) is used as dopant in a ratio of 96:4, therefore anemitting layer with a thickness of 30 nm was deposited on the emittingauxiliary layer.(1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter abbreviated as BAIq) was vacuum deposited as a holeblocking layer to a thickness of 10 nm, and Tris(8-quinolinol) aluminum(hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nmas an electron transport layer. After that, an alkali metal halide, LiFwas vacuum deposited as an electron injection layer to a thickness of0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathodeto manufacture an OLED.

To the OLEDs which were manufactured by examples and comparativeexamples, a forward bias direct current voltage was applied, andelectroluminescent (EL) properties were measured using PR-650 ofPhotoresearch Co., and T95 life was measured using a life measuringapparatus manufactured by McScience Inc. with a reference luminance of5000 cd/m². In the following table, the manufacture of a device and theresults of evaluation are shown.

Comparative Examples 35˜37

An OLED was prepared in the same manner as in Comparative Example 5except that the emitting auxiliary layer was not used and ComparativeCompound F, Comparative Compound G and Invention Compound 2-81 were usedas the hole transport layer material.

Comparative Example 38

An OLED was prepared in the same manner as in Comparative Example 5except that the emitting auxiliary layer was not used.

Comparative Examples 39˜40

An OLED was prepared in the same manner as in Comparative Example 5except that the Comparative Compound F or Comparative Compound G wereused as the emitting auxiliary layer material.

TABLE 11 Emitting Hole auxiliary Current transport layer densitybrightness Efficiency compound compound voltage (mA/cm²) (cd/m²) (cd/A)T (95) comparative comparative — 6.8 14.3  500.0 3.5 70.4 example (35)compound F comparative comparative 7.0 15.2  500.0 3.3 69.6 example (36)compound G comparative 2-81 6.9 13.5  500.0 3.7 71.2 example (37)comparative NPB — 7.3 17.9  500.0 2.8 65.3 example (38) comparativecomparative 6 .8 11.1  500.0 4.5 80.4 example (39) compound Fcomparative comparative 6 .5 10.2  500.0 4.9 81.7 example (40) compoundG example (57) 2-81  6.3 9.1 500.0 5.5 94.9 example (58) 2-83  6.2 8.6500.0 5.8 97.0 example (59) 2-85  6.1 9.2 500.0 5.4 93.2 example (60)2-86  6.2 8.9 500.0 5.6 96.9 example (61) 2-89  6.1 9.3 500.0 5.4 94.1example (62) 2-107 6.1 9.3 500.0 5.4 94.8 example (63) 2-122 6.0 9.1500.0 5.5 94.7 example (64) 2-127 6.2 8.8 500.0 5.7 96.0 example (65)2-128 6.1 8.7 500.0 5.7 95.6 example (66) 2-133 6.1 9.4 500.0 5.3 94.3example (67) 2-150 6.2 9.2 500.0 5.4 93.6 example (68) 2-151 6.0 9.4500.0 5.3 94.1 example (69) 2-152 6.0 9.1 500.0 5.5 93.7 example (70)2-153 6.1 9.4 500.0 5.3 93.2

Example 6) Manufacture and Evaluation of Green Organic Light EmittingDiode

First, on an ITO layer (anode) formed on a glass substrate,N-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine (hereinafter will be abbreviated as 2-TNATA) wasvacuum-deposited to form a hole injection layer with a thickness of 60nm. Subsequently, and on the layer,4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter will beabbreviated as NPD) was vacuum-deposited as a hole transport compound toa thickness of 60 nm to form a hole transport layer. Subsequently, theinventive compound represented by Formula (30) was vacuum-deposited asan emitting auxiliary layer material to a thickness of 20 nm to form anemitting auxiliary layer. After forming the emitting auxiliary layer, onthe emitting auxiliary layer, 4,4′-di(9H-carbazol-9-yl)-1,1′-biphenyl isused as a host, and Ir(ppy)3[tris(2-phenylpyridine)-iridium] is used asdopant in a ratio of 95:5, and an emitting layer with a thickness of 30nm was deposited.(1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter abbreviated as BAIq) was vacuum deposited as a holeblocking layer to a thickness of 10 nm, and Tris(8-quinolinol) aluminum(hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nmas an electron transport layer. After that, an alkali metal halide, LiFwas vacuum deposited as an electron injection layer to a thickness of0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathodeto manufacture an OLED.

To the OLEDs which were manufactured by examples and comparativeexamples, a forward bias direct current voltage was applied, andelectroluminescent (EL) properties were measured using PR-650 ofPhotoresearch Co., and T95 life was measured using a life measuringapparatus manufactured by McScience Inc. with a reference luminance of5000 cd/m². In the following table, the manufacture of a device and theresults of evaluation are shown.

Comparative Examples 41˜42

An OLED was prepared in the same manner as in Comparative Example 5except that Comparative Compound F or Comparative Compound G were usedas the emitting auxiliary layer material.

TABLE 12 Current density brightness Efficiency CIE compound voltage(mA/cm²) (cd/m²) (cd/A) T (95) x y comparative comparative 7.3 17.45000.0 28.7 80.4 0.30 0.61 example (41) compound F comparativecomparative 7.4 19.9 5000.0 25.1 80.9 0.33 0.64 example (42) compound Gexample (71) 2-81  5.6 11.0 5000.0 45.4 120.3 0.31 0.64 example (72)2-83  6.3 14.2 5000.0 35.1 104.3 0.31 0.64 example (73) 2-85  5.8 13.85000.0 36.2 110.1 0.34 0.61 example (74) 2-86  6.4 14.3 5000.0 35.0103.6 0.33 0.63 example (75) 2-89  6.0 14.1 5000.0 35.5 113.0 0.33 0.65example (76) 2-107 5.8 11.3 5000.0 44.3 112.6 0.32 0.65 example (77)2-122 5.9 11.4 5000.0 43.8 112.3 0.34 0.63 example (78) 2-127 6.4 12.65000.0 39.8 104.2 0.33 0.65 example (79) 2-128 6.3 12.8 5000.0 39.2102.5 0.32 0.65 example (80) 2-133 5.9 12.5 5000.0 39.9 111.2 0.32 0.65example (81) 2-150 5.4 11.4 5000.0 43.8 114.8 0.31 0.64 example (82)2-151 5.2 11.2 5000.0 44.8 111.5 0.30 0.63 example (83) 2-152 5.2 11.65000.0 43.1 112.1 0.31 0.63 example (84) 2-153 5.3 11.2 5000.0 44.8114.4 0.30 0.62

As can be seen from the results of Table 11 to 12, when OLED wasmanufactured by using the material for an organic electroluminescencedevice of the present invention as an emitting auxiliary layer material,the driving voltage of the organic electroluminescent device can belowered and the luminous efficiency and lifetime can be remarkablyimproved as compared with the comparative example not using the materialfor the emitting auxiliary layer or using the comparative compound F orthe comparative compound G.

Table 11 shows the results of the production of a blue organic lightemitting device. It can be confirmed that excellent results are obtainedwhen the compound of the present invention is used as an emittingauxiliary layer. The results of Comparative Example 39 or ComparativeExample 40 and Examples 57 to 70 show that compounds of the presentinvention substituted with specific substituents such as DBT, DBF, Cz,and Fluorene are remarkably superior to the comparative compoundssubstituted with the general aryl group even though the mother compoundis similar. That is, when specific substituents such as DBT, DBF, Cz,and Fluorene are introduced, the refractive index, the Tg, and theenergy level of the compound (HOMO, LUMO, T1, etc.) become significantlydifferent, and this difference in physical properties is a major factorin improving the device performance during device deposition (forexample, such as an energy balance), such that different device resultscan be derived.

Table 12 shows the results of the production of a green organic lightemitting device. When the compound of the present invention was used asan emitting auxiliary layer, the results were significantly superior tothe comparative compounds. This is also the effect of certainsubstituents such as DBT, DBF, Cz, and Fluorene, and a specific featureis that the superiority of the green auxiliary layer is significantlyimproved than the blue auxiliary layer. Further, in the case of the blueauxiliary layer, DBT and DBF substituted compounds showed the mostexcellent properties, but the results of the green auxiliary layershowed the best results with the Fluorene substituted compounds. Thissuggests that even if the emitting auxiliary layer compound is the same,the properties required depending on the color of the emitting layer aredifferent, so that a result which can not be deduced by those skilled inthe art can be obtained.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

1. An organic electronic element comprising an anode; a cathode; anorganic material layer formed between the anode and the cathode, whereinthe organic material layer includes an emitting layer, an hole transportlayer formed between the anode and the emitting layer, and an emittingauxiliary layer or an electron blocking layer (EBL) formed between theemitting layer and the hole transport layer, and wherein the emittingauxiliary layer or the electron blocking layer comprises a compoundrepresented by Formula (31):

wherein: R²⁰, R²¹, R²², R²³, R²⁴, and R² are each independently selectedfrom the group consisting of hydrogen; deuterium; halogen; a C₆-C₃₀ arylgroup; a fluorenyl group; a C₂-C₃₀ heterocyclic group including at leastone heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₃₀aliphatic ring and a C₆-C₃₀ aromatic ring; a C₁-C₃₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group;and a C₆-C₃₀ aryloxy group, or a plurality of R²⁰, a plurality of R²², aplurality of R²³, a plurality of R²⁴, and/or a plurality of R²⁵ may bebonded to each other to form an aromatic ring or a heteroaromatic ring,v is an integer of 0 to 3, u, w, x and y are each independently aninteger of 0 to 4, z is an integer of 0 to 5, L²⁰ and L²¹ are eachindependently a single bond; a C₆-C₃₀ arylene group; or a C₃-C₃₀heteroarylene group, Ar²⁰ is a C₆-C₃₀ aryl group; or a C₃-C₃₀heteroarylene group, X²⁰ is O, S, NR′ or CR′R″, wherein R′ and R″ areeach independently selected from the group consisting of a C₁-C₃₀ alkylgroup; a C₆-C₃₀ aryl group; a C₃-C₃₀ heterocyclic group including atleast one heteroatom of O, N, S, Si, or P; and R′ and R″ may be bondedto each other to form a spiro ring.
 2. The organic electronic elementaccording to claim 1, wherein the moiety

in Formula (31) is represented by:

wherein R²⁰, R²⁵, X²⁰, L²¹, u and v are the same as defined in claim 1.3. The organic electronic element according to claim 1, wherein thecompound represented by Formula (31) is selected from the groupconsisting of the following compounds:


4. The organic electronic element according to claim 1, wherein thecompound represented by Formula (31) is used as a green emittingauxiliary layer material.
 5. A display device comprising the organicelectronic element of claim 1; and a control part driving the displaydevice.
 6. The display device according to claim 5, wherein the organicelectronic element is an OLED, an organic solar cell, an organic photoconductor (OPC), organic transistor (organic TFT), or an element formonochromic or white illumination.